A friend recently shared the parable of the businessman and the fisherman with me. If you’ve never heard it, the story goes something like this:
A wealthy businessman comes across a fisherman relaxing after the day’s catch. The businessman asks why he isn’t out catching more fish. The fisherman explains that he has already caught enough. The businessman launches into a grand plan. Catch more fish. Buy a bigger boat. Build a fleet. Open a processing plant. Become wealthy. Sell the company.
“And then what?” the fisherman asks.
“Then,” the businessman replies, “you can retire. Relax. Spend time with your family. Take naps. Fish when you want.”
The fisherman smiles. “I’m already doing that.”
It’s a clever story, and like most good parables, it creates a little discomfort. Most of us can see ourselves in both characters. But I also think the story presents a false choice.
The implication is that you either spend your life endlessly chasing success or you reject ambition altogether. I don’t think either is quite right.
We Were Made to Be Productive
One of the biggest misconceptions about retirement is that the goal is to stop working. In my experience, that’s almost never what happy retirees actually do. The happiest retirees I know stay busy.
They babysit grandchildren.
They volunteer at church.
They coach little league.
They serve at the food bank.
They mentor younger people.
They build things.
They fix things.
They garden.
They help neighbors.
They’re productive.
The difference is that they get to choose where they invest their effort. That’s a very different thing than idleness.
I don’t believe we’re designed to spend decades doing nothing. There is something deeply satisfying about looking back at the end of the day and saying, “I built that.” Or “I helped with that.” Or “That person is better because I invested in them.”
Modern work sometimes makes that difficult to see. Many careers can feel like answering emails, attending meetings, and moving numbers around a spreadsheet. There is certainly value in those jobs—I have one—but they don’t always provide the tangible satisfaction of seeing what your effort produced.
That’s one reason I think so many people find fulfillment in coaching, volunteering, woodworking, gardening, serving at church, or helping with their grandchildren. We were made to create, improve, and contribute.
But We Also Need to Know What “Enough” Looks Like
The danger isn’t ambition. The danger is restlessness.
If “enough” is always another promotion, another $500,000, another rental property, or another five years of work, then enough never arrives.
I’ve seen people postpone the life they wanted for years because they convinced themselves that just a little more would finally bring security. Sometimes another five years really is the right decision. Sometimes it isn’t.
The math can tell us whether you can retire. It can’t tell you whether you should.
What Are You Retiring To?
When clients tell me they’re financially able to retire, I rarely start by talking about money. Instead, I ask a different question:
What are you retiring to?
If you love your work, perhaps retirement isn’t the answer yet. Maybe mentoring younger employees or intentionally preparing your successor would make the next chapter even more meaningful.
If you’re excited to spend Tuesdays with your grandkids, volunteer in your community, travel with your spouse, or coach your grandson’s baseball team, that’s a different conversation.
You are not simply escaping from work. You are moving toward something more meaningful than what you’re leaving behind.
When people retire from something without retiring to something, that’s often where they struggle.
A Lesson From Our Summer Vacation
Our family recently spent nearly two weeks camping through Yellowstone, Grand Teton, the Badlands, and several other national parks.
There were eight of us. We slept in tents. We cooked most of our own meals.
The trip wasn’t extravagant. In fact, national parks remain one of the best values in family travel. You don’t need a luxury budget to stand in front of the Tetons at sunrise or watch your kids jump into a mountain lake.
What struck me most wasn’t the scenery—although it was incredible. It was how present I felt.
When I’m on those trips, I’m not thinking about email or the next meeting. I’m completely engaged in the moment. Hiking with my kids. Setting up camp. Watching wildlife. Jumping into cold lakes. Laughing around the campfire.
And because I’m fully there, my kids get a better version of me.
Looking back, I don’t think what made the trip meaningful was that we could afford it. It was that we had built a life with enough margin to actually experience it.
The Mean Between Two Extremes
Aristotle believed that virtue often exists between two extremes. I think contentment works much the same way. On one side is endless striving—the belief that happiness is always waiting on the next achievement. On the other side is apathy—the belief that comfort alone is enough.
Neither leads to a particularly meaningful life.
Work matters. Achievement matters. Building something worthwhile matters.
But so do dinners around the table, coaching your kids, serving your church, taking the trip you’ve been talking about for years, and investing in the people you love.
The goal isn’t to avoid hard work. The goal is to make sure your hard work is serving the life you actually want to live.
Because in the end, wealth isn’t simply having more money.
It’s having enough freedom to spend your life doing work worth doing alongside people you love.
That strikes me as a far better definition of success than either the businessman or the fisherman offered.
This post is for education and entertainment purposes only. Nothing should be construed as investment, tax, or legal advice.